20,034

Dukes County, MA Homes

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  • /7

    $3,100,000

    • Land
    • 3.04 Acres
    • $1,019,737 per Acre

    114 Meeting House Way Unit 7, Edgartown, MA 02539

    3 Acre Katama Building Lot with Existing Guest House.This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South

    Rose Ryley Wallace & Co. Sotheby's

    114 Meeting House Way Unit 7, Edgartown, MA 02539
  • /17

    $12,000 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • House for Rent

    223 Sandpiper Lane Vh405, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open

    Karen Overtoom Karen M. Overtoom R.E.

    223 Sandpiper Lane Vh405, Tisbury, MA 02568
  • /37

    $7,289,000 Sold Oct 15, 2025

    25 Osprey Ln, Chilmark, MA 02535

    • 4 Beds
    • 5 Baths
    • 3,777 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $1,930/SF
    • 77 Days On Market

    Current Estimated Value $6,307,216

    Last Listing Agent Deb Hancock Hancock Real Estate

    25 Osprey Ln, Chilmark, MA 02535
    • /42

      Not Listed For Sale

      • 6 Beds
      • 8 Baths
      • 4,617 Sq Ft

      11 Cummings Way, Edgartown, MA 02539

      11 Cummings Way, Edgartown, MA 02539
  • /4

    $625,000

    • Land
    • 0.34 Acre
    • $1,815,277 per Acre

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

    Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

    Andrew McElhinney Compass LLC

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
  • /40

    $32,500 total monthly price

    • 6 Beds
    • 4.5 Baths
    • 3,222 Sq Ft
    • House for Rent

    100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

    Karen Overtoom Karen M. Overtoom R.E.

    100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
  • /32

    $1,100,000 Sold Jun 27, 2025

    10 Kims Way, Oak Bluffs, MA 02568

    • 4 Beds
    • 2.5 Baths
    • 1,976 Sq Ft
    • Built 1985

    Last Sold Summary

    • 12% Below List Price
    • $557/SF
    • 156 Days On Market

    Last Listing Agent Michael Schweikert Ocean Park Realty, Inc.

    10 Kims Way, Oak Bluffs, MA 02568
    • /32

      Est $4,514,456 Not Listed For Sale

      • 5 Beds
      • 8 Baths
      • 5,305 Sq Ft

      225 Bigelow Rd, Vineyard Haven, MA 02568

      225 Bigelow Rd, Vineyard Haven, MA 02568
  • /29

    $1,725,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,600 Sq Ft

    654 Lighthouse Rd, Aquinnah, MA 02535

    Waterview beach house in Aquinnah. Just a short deeded walking path to the calm and sandy shores of the North Shore. The traditional layout features the kitchen, living room, dining room, and a full bath on the first floor. The living room offers water views, a cozy fireplace, and multiple sliding doors leading out to the wrap-around porch. Upstairs, the views are even more stunning! There are

    Heidi Vanderhoop Tea Lane Associates

    654 Lighthouse Rd, Aquinnah, MA 02535
  • /33

    $22,000 total monthly price

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    2 Strikers Way Ch211, Chilmark, MA 02535

    SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable drip coffee maker with glass carafe. There is a coffee grinder provided in the

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, Chilmark, MA 02535
  • /22

    $435,000 Sold Aug 26, 2025

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535

    • Land
    • 0.1 Acre
    • $4,350,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 18 Days On Market

    Last Listing Agent Emma Kiley Bryant Landmarks at TODAY Real Estate

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    • /7

      Est $5,203,243 Not Listed For Sale

      • 6 Beds
      • 7 Baths
      • 6,783 Sq Ft

      3 Duarte Cir, Edgartown, MA 02539

      3 Duarte Cir, Edgartown, MA 02539
  • /9

    $2,450,000

    • Land
    • 5.37 Acres
    • $456,238 per Acre

    9 Maqua Way, Edgartown, MA 02539

    Chappaquiddick: Beautiful 5-acre parcel offering private frontage on Katama Bay. The generous-sized lot affords plenty of development flexibility, with the ability to capture the view from nearly any location. Located on Maqua Way, a quiet subdivision just off the paved road, the property is conveniently situated near all the Chappy favorites: beaches, trails, a community center, and Slip Away

    Katherine Donahue Sandpiper Realty Inc

    9 Maqua Way, Edgartown, MA 02539
  • /20

    $16,800 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • House for Rent

    31 S Ridge Rd Ch218, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

    Karen Overtoom Karen M. Overtoom R.E.

    31 S Ridge Rd Ch218, Chilmark, MA 02535
  • /2

    $5,375,000 Sold Nov 14, 2025

    37 Morse St, Edgartown, MA 02539

    • 4 Beds
    • 5.5 Baths
    • 2,911 Sq Ft
    • Built 1820

    Last Sold Summary

    • $1,846/SF
    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    37 Morse St, Edgartown, MA 02539
    • /20

      Est $1,757,793 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,971 Sq Ft

      21 Bold Meadow Ln, Edgartown, MA 02539

      21 Bold Meadow Ln, Edgartown, MA 02539
  • /15

    $2,490,000

    • Land
    • 7.2 Acres
    • $345,833 per Acre

    3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539

    Build your dream home on the special 7.2 acre North lot 1 private wooded property with 1/2 ownership in the beautiful 4.5 acre meadow in the grand Boldwater Association(BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all

    Robert Kenney Tea Lane Associates

    3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539
  • /31

    $40,000 total monthly price

    • 6 Beds
    • 6 Baths
    • 3,960 Sq Ft
    • House for Rent

    384 Middle Rd Ch222, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

    Karen Overtoom Karen M. Overtoom R.E.

    384 Middle Rd Ch222, Chilmark, MA 02535
  • /19

    $1,095,000 Sold May 02, 2025

    31 Davis St, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,945 Sq Ft
    • Built 1966

    Last Sold Summary

    • 2% Above List Price
    • $563/SF
    • 5 Days On Market

    Current Estimated Value $1,165,193

    Last Listing Agent Sheila Morse Island Real Estate

    31 Davis St, Vineyard Haven, MA 02568
    • /32

      Est $2,845,528 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,101 Sq Ft

      10 Codman Spring Rd, Edgartown, MA 02539

      10 Codman Spring Rd, Edgartown, MA 02539
  • /25

    $799,000

    • 2 Beds
    • 1 Bath
    • 861 Sq Ft

    24 School St, Oak Bluffs, MA 02557

    An unbeatable location ~ just a short distance to the harbor, beaches, ferry ports, the public library, and all the vibrant attractions of Oak Bluffs. This 2-bedroom, 1-bathroom ranch-style home is sited on a 10,454 sf level lot with a detached garage/shed. The property offers one-floor living, a convenient location, and great potential. The main living area includes an open living and dining

    Stephanie Roache Donnelly + Co

    24 School St, Oak Bluffs, MA 02557
  • /32

    $42,000 total monthly price

    • 5 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    19 Lake Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms,

    Karen Overtoom Karen M. Overtoom R.E.

    19 Lake Rd, Chilmark, MA 02535
  • /2

    $1,645,000 Sold Feb 21, 2025

    49 Oak Ln, West Tisbury, MA 02575

    • 4 Beds
    • 3.5 Baths
    • 2,576 Sq Ft
    • Built 1974

    Last Sold Summary

    • 10% Above List Price
    • $639/SF
    • 6 Days On Market

    Last Listing Agent Dawn Bellante Sandpiper Realty Inc

    49 Oak Ln, West Tisbury, MA 02575
    • /19

      Est $1,371,490 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,520 Sq Ft

      46 Windsor Dr, Edgartown, MA 02539

      46 Windsor Dr, Edgartown, MA 02539
  • /43

    $14,500,000

    • 4 Beds
    • 4.5 Baths
    • 3,705 Sq Ft

    64 Squibnocket Farm Rd, Chilmark, MA 02535

    Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

    Thomas Wallace Wallace & Co. Sotheby's

    64 Squibnocket Farm Rd, Chilmark, MA 02535
  • /35

    $22,000 total monthly price

    • 4 Beds
    • 2 Baths
    • 2,290 Sq Ft
    • House for Rent

    36 Henry Hough Lane Ch206, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

    Karen Overtoom Karen M. Overtoom R.E.

    36 Henry Hough Lane Ch206, Chilmark, MA 02535
  • /2

    $505,000 Sold Sep 26, 2025

    02 John Hoft Rd Unit 2, Tisbury, MA 02568

    • Land
    • 1.3 Acres
    • $388,462 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 120 Days On Market

    Last Listing Agent Tony Tobia Tobia Real Estate, LTD

    02 John Hoft Rd Unit 2, Tisbury, MA 02568
    • /22

      Est $4,449,670 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,905 Sq Ft

      1 Skippers View Ln, Aquinnah, MA 02535

      1 Skippers View Ln, Aquinnah, MA 02535
  • /7

    $795,000 Pending

    • Land
    • 2.52 Acres
    • $315,476 per Acre

    0 W End Rd, Gosnold, MA 02713

    Vacant, buildable, water-view lot comprised of 2.52 ± wooded acres with subdivision potential and views of Martha’s Vineyard and Vineyard Sound. Buyer should do their own due-diligence on subdivision. Located on Cuttyhunk Island, part of the Elizabeth Islands off the southern coast of Massachusetts is located between Buzzards Bay and Vineyard Sound. At just 550± acres Cuttyhunk Island offers a

    Slater Anderson LandVest, Inc.

    0 W End Rd, Gosnold, MA 02713
  • /39

    $110,000 total monthly price

    • 5 Beds
    • 5 Baths
    • 4,000 Sq Ft
    • House for Rent

    17 Round Pond Rd Ch240, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Round Pond Rd Ch240, Chilmark, MA 02535
  • /38

    $1,500,000 Sold Jan 23, 2026

    128 W Spring St, Vineyard Haven, MA 02568

    • 5 Beds
    • 3.5 Baths
    • 2,436 Sq Ft
    • Built 2013

    Last Sold Summary

    • 14% Below List Price
    • $616/SF
    • 145 Days On Market

    Last Listing Agent David Dickinson Compass

    128 W Spring St, Vineyard Haven, MA 02568
    • /2

      Est $1,806,607 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,250 Sq Ft

      11 Deacon Vincent Way, Edgartown, MA 02539

      11 Deacon Vincent Way, Edgartown, MA 02539
  • /7

    $1,575,000

    • 2 Beds
    • 1 Bath
    • 924 Sq Ft

    47 Quenames Rd, Chilmark, MA 02535

    On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural

    Dawn Bellante Sandpiper Realty, Inc.

    47 Quenames Rd, Chilmark, MA 02535
  • /19

    $24,000 total monthly price

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    44 Flanders Ln, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

    Karen Overtoom Karen M. Overtoom R.E.

    44 Flanders Ln, Chilmark, MA 02535
  • /42

    $1,700,000 Sold Nov 03, 2025

    35 Tower Ridge Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 4 Baths
    • 2,558 Sq Ft
    • Built 1986

    Last Sold Summary

    • 20% Below List Price
    • $665/SF
    • 118 Days On Market

    Current Estimated Value $1,741,804

    Last Listing Agent Katherine Donahue Sandpiper Realty Inc

    35 Tower Ridge Rd, Oak Bluffs, MA 02557
    • /39

      Est $7,322,137 Not Listed For Sale

      • 5 Beds
      • 6 Baths
      • 6,546 Sq Ft

      103 Main St, Vineyard Haven, MA 02568

      103 Main St, Vineyard Haven, MA 02568
  • /14

    $835,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    51 Lantern Ln, Vineyard Haven, MA 02568

    Find your sweet spot in this charming starter home, ideally located on a quiet street yet within an effortless walk of everything. Forget the car and get your steps in! You're a short jaunt to essentials like Cronig's Market and Shirley's Hardware, AND local favorites including The Maker, Black Dog Cafe, Island Fresh Pizza, Pie Chicks, and Island Adventures Mini Golf. Also within walking distance

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

    51 Lantern Ln, Vineyard Haven, MA 02568
  • /32

    $36,000 total monthly price

    • 3 Beds
    • 3.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    29 Cemetery Rd Ch216, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

    Karen Overtoom Karen M. Overtoom R.E.

    29 Cemetery Rd Ch216, Chilmark, MA 02535
  • /30

    $1,995,000 Sold Aug 29, 2025

    26 Box Turtle Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 3.5 Baths
    • 2,891 Sq Ft
    • Built 1980

    Last Sold Summary

    • $690/SF
    • 5 Days On Market

    Current Estimated Value $2,194,577

    Last Listing Agent Jayne Isford Ocean Park Realty Inc

    26 Box Turtle Ln, Oak Bluffs, MA 02557
    • /34

      Est $1,627,852 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,452 Sq Ft

      84 Christiantown Rd, Vineyard Haven, MA 02568

      84 Christiantown Rd, Vineyard Haven, MA 02568

Showing Results 161 - 200, Page 5 of 18

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